Triethylamine → 2-Chloro-n-(1-methylethyl)-n-propyl-6-(trimethylsilyl)benzamide

HRID 1458070Notes

Reaction equation

HRID 1458070 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([Si:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[C:11](Cl)=[O:12].Cl.[CH2:23]([NH:26][CH:27]([CH3:29])[CH3:28])[CH2:24][CH3:25]>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([Si:18]([CH3:21])([CH3:20])[CH3:19])[C:10]=1[C:11]([N:26]([CH:27]([CH3:29])[CH3:28])[CH2:23][CH2:24][CH3:25])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13344554(Propan-2-yl)(propyl)amine hydrochlorideHCID 151835572-Chloro-6-(trimethylsilyl)benzoyl chloride

Product 1

HCID 186303012-Chloro-n-(1-methylethyl)-n-propyl-6-(trimethylsilyl)benzamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (27.89 mL, 200 mmol) was added to a mixture of the compound of Example b (2.47 g, 10 mmol) and N-propyl-N-iso-propylamine hydrochloride (~ 92 mmol) in toluene (100 mL). The reaction was stirred overnight at ambient temperature, then was partitioned between ethyl acetate and dilute citric acid. The organic phase was washed with brine, dried (MgSO4), and concentrated to afford 2.50 g of the title compound as a waxy amber solid, an 80% yield.

Workup

  1. customwas partitioned between ethyl acetate and dilute citric acid
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c743adf10359411bbf1ee4d4f20fa4e7
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Reaction notes

Loading…